coulda woulda shoulda

Gay guys recollect the high school romances and hookups that got away

Teenage boy sitting alone on bleachers

Not every gay gets a Heartstopper-level romance in high school—or a chance to experiment, even. And on Reddit, adults are looking back at the near-misses from those years.

The conversation kicked off as one r/askgaybros user asked other Redditors if they ever thought back to high school and wondered whether a guy was asking them out on a date.

“When I was in high school, there was this guy who would teach me to fight [and] put someone to the ground just so I could stand up for myself,” that user wrote.

“He was a gym guy. We didn’t talk much. I was sitting outside the school and he walked up to me and asked me if I was interested in going to a concert. I wasn’t out and had lots of friends, and when we [were] play-fighting I was thinking I feel something but was not 100%. [It took] me five years to pick up on this.”

Soon other gays began to share their stories of emotional missed connections from their queer youth.

Here are other tales from the thread:

“In high school, I finally found other gay friends. Junior year, I transferred to a choice school. To get in, I had to be interviewed. The interview panel was two students and a teacher. One of the students was gay and could tell I was, too. My dad and the teacher left, and the first thing out his mouth was to ask me if I’m gay. We’ve been homies ever since. It was very fun. We had a little group of other gay kids, and we had nicknamed ourselves after the Plastics from Mean Girls. It was a very small school—our senior class had 26 students total, and only 13 graduated on time. To this day, I keep in contact with all of them. Those are my bitches—I love them. As far as attention from guys, zero romantic encounters. I got to mess around with a few of the guys I had my eyes on over time. [Around] 4 of the guys I found attractive, including my brother’s best friend. And one of the guys I really had the hots for.”

“It was a writing project in 11th grade. We had to pair up with people and write about each other’s skills and talents. My partner’s skills were his big, 8-inch dick. He wouldn’t drop the dick thing for like 15 minutes. I wasn’t out of the closet, but I was frequently called a f*g and stuff. Maybe it was flirting, maybe it wasn’t, but it was the closest to flirting I ever got (with a guy, in real life, as a teenager). It’s pretty pathetic and sad that a straight guy bragging about his dick as a joke for a few minutes is the only thing I got my entire high school career. That extreme loneliness is gay trauma. I really, really, really wanted to see his dick.”

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“FWIW, I didn’t get anything in high school either. It was a soul-crushingly lonely time for me. Really didn’t participate in anything, never went to a dance or a party, nada. I can relate. I did find out long after the fact, however, that another boy a year or two younger than me apparently was hot for me back in high school. He messaged me when I was 40 years old and confessed how he’d felt when we were teens. I’d had no idea. He also wanted to hook up and sort of fulfill the fantasy retroactively while he was back in town visiting family, but I had houseguests that weekend and couldn’t really swing it. When he messaged me, I was like, dammit… I could’ve been having sex in high school if only I’d known.”

“I do think back sometimes and wonder… When I was in high school—I think I was a junior at the time—me and this other guy were being weighed. He asked the coach a question about [the weighing] being more accurate if we were nude. Then he told me that he’d do it if I’d do it. Before I could say anything, the coach interjected and said, ‘No, we’re not doing that.’ Sometimes I think about that.”

“My sometimes-bully-sometimes-friend would ask me to sleep over a lot. Things would always be very charged and blatant. But I was too in the closet to reciprocate.” 

“I’m 80% sure I could have gotten tag-teamed by my crushes, but who knows.”

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